Month: April 2021

Synthetic Route of 78531-29-0,Some common heterocyclic compound, 78531-29-0, name is 1,3-Dimethoxypropan-2-amine, molecular formula is C5H13NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Intermediate 222: (4-((1,3-Dimethoxypropan-2-yl)amino)-3-nitrophenyl)methanol To a solution of (4-fluoro-3-nitrophenyl)methanol (16 g, 93 mmol) in THF (80 mL) was added 1,3- dimethoxypropan-2-amine (10 g, 84 mmol) and DIPEA (15 mL, 86 mmol). The mixture was split into seven portions and heated under microwave conditions at 100 C for 7 hours. The reaction mixture was partitioned between ethyl acetate (3 x 500 mL) and saturated aqueous sodium bicarbonate solution (750 mL). The organic layers were combined, washed with saturated brine (500 mL), and evaporated under reduced pressure. The sample was loaded in dichloromethane and purified SPE (silica, 100 g) using a gradient of 0-80% EtOAc in cyclohexane. The appropriate fractions were combined and evaporated under reduced pressure to give a the title compound (12.0 g, 44.4 mmol). LCMS (System B): tRET = 0.85 min, MH+ = 271. Less pure fractions were combined and evaporated. The sample was loaded in dichloromethane and purified by SPE (silica, 100 g) using a gradient of 0- 50 % EtOAc in cyclohexane. The appropriate fractions were combined and evaporated under reduced pressure to give the title compound (3.7 g, 13.69 mmol). LCMS (System J): tRET = 0.85 min, MH+ = 271.

The synthetic route of 78531-29-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BIT, Rino Antonio; BROWN, John Alexander; HUMPHREYS, Philip G.; JONES, Katherine Louise; (240 pag.)WO2016/146738; (2016); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 2357-52-0, name is 4-Bromo-2-fluoroanisole, A new synthetic method of this compound is introduced below., Formula: C7H6BrFO

General procedure: To a solution of compound 1a-e (10.0 mmol,1.0 eq) in anhydrousTHF (20 mL) was slowly added n-BuLi (6 mL of 2.5 M solution inhexane, 15.0 mmol, 1.5 eq) at 78 C. The mixture was stirred for1 h and triisopropyl borate (50.0 mmol, 5.0 eq) was added by syringe.The solutionwas stirred for another 1 h and allowed towarmto 25 C overnight. The reactionwas cooled to 0 C, followed by thesequential addition ofwater (5 mL) and 2N HCl (5 mL). After 10 min,an additional 35 mL of 2N HCl was added and the mixture wasfurther stirred for 30 min. The mixture was extracted with ethylacetate (20 mL * 3) and the combined organic layers wereconcentrated to a thick oil under reduced pressure. Crystallizationwith cold hexane yielded a white solid.

The synthetic route of 2357-52-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sang, Yali; Han; Pannecouque, Christophe; De Clercq, Erik; Zhuang, Chunlin; Chen; European Journal of Medicinal Chemistry; vol. 182; (2019);,
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Synthetic Route of 109-85-3,Some common heterocyclic compound, 109-85-3, name is 2-Methoxyethylamine, molecular formula is C3H9NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

4-Amino-N-hydroxy-1,2,5-oxadiazole-3-carboximidoyl chloride (200.0 g, 1.23 mol) was mixed with ethyl acetate (1.2 L). At 0-5 C. 2-methoxyethylamine [Aldrich, product No.143693] (119.0 mL, 1.35 mol) was added in one portion while stirring. The reaction temperature rose to 41 C. The reaction was cooled to 0-5 C. Triethylamine (258 mL, 1.84 mol) was added. After stirring 5 min, LCMS indicated reaction completion. The reaction solution was washed with water (500 mL) and brine (500 mL), dried over sodium sulfate, and concentrated to give the desired product (294 g, 119%) as a crude dark oil. LCMS for C6H12N5O3 (M+H)+: m/z=202.3. 1H NMR (400 MHz, DMSO-d6): delta 10.65 (s, 1H), 6.27 (s, 2H), 6.10 (t, J=6.5 Hz, 1H), 3.50 (m, 2H), 3.35 (d, J=5.8 Hz, 2H), 3.08 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Methoxyethylamine, its application will become more common.

Reference:
Patent; Incyte Corporation; Incyte Holdings Corporation; Combs, Andrew P.; Yue, Eddy W.; Sparks, Richard B.; Zhu, Wenyu; (63 pag.)US9320732; (2016); B2;,
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Electric Literature of 54149-17-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 66 Preparation of (4bR,8aR,9R)-N-(3-(2-(2-methoxyethoxy)ethoxy)pyridin-4-yl)-ll- methyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthren-3-amine (66), hydrochloride salt Step 1. Synthesis of 4-chloro-3-(2-(2-methoxyethoxy)ethoxy)pyridine, A mixture of 4-chloropyridin-3-ol (100 mg, 0.772 mmol), l-bromo-2-(2- methoxyethoxy)ethane (141 mg, 0.772 mmol) and CS2CO3 (503 mg, 1.544 mmol) in dimethylacetamide (5 mL) was irradiated in a microwave at 120 C for two hours. The reaction mixture was cooled to room temperature and poured into 20 mL of water. The aqueous solution was extracted with ethyl acetate 3×20 mL. The organic layer was combined, was washed with brine (50 mL), was dried over anhydrous sodium sulfate, was filtered and was concentrated. The crude product was purified via flash column chromatography on silica gel to afford 4-chloro-3-(2-(2-methoxyethoxy)ethoxy pyridine (87.4 mg, 48.9%). MS (EI) for C10H14CINO3: 232.0 (MH+).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Bromo-2-(2-methoxyethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEKTAR THERAPEUTICS; ANAND, Neel; AURRECOECHEA, Natalia; CHENG, Lin; DENG, Bo-liang; O’MAHONY, Donogh; MU, Yongqi; KROGH-JESPERSEN, Erik; (215 pag.)WO2016/182840; (2016); A1;,
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These common heterocyclic compound, 2752-17-2, name is 2,2′-Oxydiethanamine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 2,2′-Oxydiethanamine

14.2) N,N’-(oxydiethane-2,1-diyl)bis(5-methoxy-4-nitro-1,3-benzothiazole-2-carboxamide) 3.03 g (6.5 mmol; 1.1 eq.) of bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBroP) is added to 1.5 g (5.9 mmol) of 5-methoxy-4-nitro-1,3-benzothiazole-2-carboxylic acid and 1.13 ml (6.5 mmol; 1.1 eq.) of diisopropylethylamine in solution in 100 ml of dichloromethane. The reaction mixture is maintained for 10 minutes under stirring at ambient temperature, then 0.31 g (2.9 mmol; 0.5 eq.) of 2.2′-oxybis(ethylamine) and a spatula tip’s worth of dimethylaminopyridine are added to the medium which is maintained under stirring for 18 hours at ambient temperature. The insoluble matter is filtered and the solvent is evaporated off under reduced pressure. The residue is then purified on a silica column (eluent:ethyl acetate/heptane: 4/1) and 250 mg of expected product (yield=8%) is obtained in the form of beige powder. MS-LC: MH+=577.11; r.t.=10.27 min.

The synthetic route of 2,2′-Oxydiethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Galcera-Contour, Marie-Odile; Prevost, Gregoire; Sidhu, Alban; US2007/244186; (2007); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1663-61-2, name is (Triethoxymethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of (Triethoxymethyl)benzene

General procedure: The 2-aminobenzamide (1 equiv), the orthoester (2?3 equiv) and absolute ethanol (2?3 mL) wereplaced in a 15-mL Chemglass screw-cap pressure tube (No. CG-1880-01, Chemglass, Vineland, NJ,USA). Glacial acetic acid (3 equiv) was added, N2 was introduced to the vessel and the cap wastightened. The vessel was heated at 110 ¡ãC for 12?72 h, then cooled and concentrated to give thequinazolinone, which was purified by crystallization from absolute ethanol or trituration from 5percentether in pentane. The following compounds were prepared:

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1663-61-2.

Reference:
Article; Gavin, Joshua T.; Annor-Gyamfi, Joel K.; Bunce, Richard A.; Molecules; vol. 23; 11; (2018);,
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Application of 1663-61-2, The chemical industry reduces the impact on the environment during synthesis 1663-61-2, name is (Triethoxymethyl)benzene, I believe this compound will play a more active role in future production and life.

The product of Example 33D (62 mg, 0.2 mmol) was treated with triethyl orthobenzoate (Aldrich, 0.5 ml_) in DMF (1 ml_) at 1000C for 10h. It was then concentrated. The title product was purified by preparative HPLC (Xterra.(TM)., column, Xterra RP-18, 5 mum, 30 x 100 mm. Eluting Solvent, MeCN / H2O (NH4HCO3, 0.1 M, pH=10), (v. 90/10 to 10/90 over 20 min.) Flow rate, 75 mL/min., uv, 250 nm) as solid (40.0 mg, 50percent). 1H NMR (500 MHz, CD3OD) delta 1.52 – 1.64 (m, 1 H), 1.68 – 1.80 (m, 1 H), 1.80 – 1.92 (m, 1 H), 2.06 – 2.18 (m, 1 H), 2.25 – 2.31 (m, 1 H), 2.75 – 3.10 (m, 5 H), 3.39 – 3.49 (m, 1 H), 5.14 – 5.27 (m, 1 H), 7.55 – 7.66 (m, 3 H), 7.69 (dd, J=8.5, 1.8 Hz, 1 H), 7.81 (d, J=8.2 Hz, 1 H), 8.00 (d, J=1.5 Hz, 1 H), 8.27 (dd, J=8.1 , 1.7 Hz, 2 H), 8.89 (s, 2H) ppm; MS (DCI/NH3): 399 (M+H)+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, (Triethoxymethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; WO2006/65233; (2006); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 17061-62-0 as follows. Recommanded Product: Bis(4-methoxybenzyl)amine

To a solution of 2-chloroethanesulfonyl chloride (2mL, 19 mmol) in dichloromethane (95 mL) was added dropwise triethylamine (2.64 mL, 19 mmol) at -72C under argon. The resulting mixture was stirred at this temperature for 10 min. Then the reaction mixture was warmed to room temperature and stirred for 2h. After this time bis-(4-methoxybenzyl)-amine (4.94 g, 19 mmol) and TEA (3.17 mL, 23 mmol) were added at 0C. After stirring at room temperature for 2 h the solvent was evaporated to give 6.87 g of the crude product (100%). 1H NMR (700 MHz, Chloroform-d) delta 7.27 – 7.19 (m, 4H), 6.93 – 6.88 (m, 4H), 6.32 (dd, J = 16.5, 9.8 Hz, 1H), 6.22 (d, J = 16.5 Hz, 1H), 5.87 (d, J = 9.8 Hz, 1H), 4.22 (s, 4H), 3.84 (s, 6H). The crude product was used to the next step without any further purification.

According to the analysis of related databases, 17061-62-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ONCOARENDI THERAPEUTICS SP. Z O.O.; B?ASZCZYK, Roman; BRZEZI?SKA, Joanna; GO??BIOWSKI, Adam A.; OLCZAK, Jacek; (93 pag.)WO2016/108707; (2016); A1;,
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Some common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 4-Isopropoxyaniline

Synthesis of compound 126.1. To a solution of 2.5 (0.30 g, 0.96 mmol, 1.0 eq) in dry CH3CN (5mL) were added 4-isopropoxyaniline (0.145g, 0.96mmol, l .Oeq), and DIPEA (0.49 mL, 2.88 mmol, 3. Oeq). Reaction mixture was allowed to stir at 100 C for 24 hours. After completion of the reaction, the mixture was cooled to room temperature. Water (10 mL) was added to the mixture and extracted with EtOAc. Organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure to give crude which was purified by column chromatography to afford compound 126.1 (0.300g, 73.15%). MS (ES): m/z = Ml A [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7664-66-6, its application will become more common.

Reference:
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; WO2015/131080; (2015); A1;,
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Electric Literature of 707-07-3,Some common heterocyclic compound, 707-07-3, name is (Trimethoxymethyl)benzene, molecular formula is C10H14O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL¡Á3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Trimethoxymethyl)benzene, its application will become more common.

Reference:
Article; Kim, Jaeho; Kim, Jihye; Lee, Hyunseung; Lee, Byung Min; Kim, Byeong Hyo; Tetrahedron; vol. 67; 41; (2011); p. 8027 – 8033;,
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